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TwentyTwenty

Dir, Engineering

Lead the engineering organization for Pathfinder, Twenty's core cyber operations platform. Manage engineering managers, drive org design and technical roadmap in partnership with PM, engage on architecture with senior ICs, and ensure high-quality delivery for cloud and on-prem deployments. Requires 8+ years software engineering and 5+ years engineering management experience including managing managers.

About the job

Responsibilities

  • Own engineering execution across the Pathfinder product: delivery, quality, and technical accountability across all teams.
  • Lead, develop, and hold accountable a set of engineering managers; build their capacity to run their teams independently.
  • Drive org design decisions: team scope, composition, sequencing of team splits, and addition of new management capacity as the org grows.
  • Balance engineering capacity across teams; make explicit prioritization calls when demand exceeds supply.
  • Own the technical roadmap in partnership with the Pathfinder Product Manager.
  • Engage at the architecture level with senior ICs—reviewing designs, providing guidance, and ensuring technical coherence across the platform.
  • Supervise hiring across all Pathfinder engineering teams: set the bar, calibrate across managers, and close strong candidates.
  • Partner with the VP of Engineering on org strategy, headcount planning, and cross-product engineering initiatives.
  • Communicate clearly to senior leadership on progress, risks, and tradeoffs across the Pathfinder roadmap.
  • Ensure engineering practices—security, quality, reliability, and operational discipline—meet the standards required for mission-critical deployments.

Requirements

  • 8+ years of professional software engineering experience.
  • 5+ years of engineering management experience, including at least 3 years managing other engineering managers.
  • Track record of owning engineering execution across multiple teams simultaneously, with high quality and clear accountability.
  • Architectural judgment to engage credibly with senior ICs: reviewing designs, identifying risks, and providing technical guidance across a complex, multi-layer stack.
  • Experience owning org design decisions: team structure, scope boundaries, and how to sequence growth as headcount scales.
  • Experience managing engineering organizations serving both cloud-hosted and on-premises or customer-controlled deployment environments.
  • Experience partnering with product managers to translate operational requirements into technical roadmaps and delivery plans.
  • Experience supervising hiring across multiple teams: setting the bar, calibrating across managers, and running a structured, high-signal process.
  • Must be eligible to obtain a U.S. Government security clearance.

Nice-to-Haves

  • Experience in defense, intelligence, or national security technology environments.
  • Led engineering organizations building operational platforms for government or mission-critical customers.
  • Worked with graph databases or graph-based modeling for complex analytical problems.
  • Led teams shipping enterprise features: multi-tenancy, RBAC, audit logging, or similar.
  • Experience with secure development practices for government or controlled environments.
  • Scaled an engineering organization through a rapid growth phase, including adding management layers.

Tech Environment

  • React + TypeScript for user-facing applications and shared UI components
  • Go (and sometimes Python) for backend services and integrations
  • Neo4j and graph-based data modeling for core platform capabilities
  • PostgreSQL, Terraform, Ansible, and infrastructure-as-code
  • AWS, Docker, Kubernetes, CI/CD, and observability tooling
  • Customer private cloud deployment and on-site operational environments

Skills

React, TypeScript, Go, Python, Neo4J, Postgres, Terraform, Ansible, AWS, Docker, Kubernetes, CI/CD

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